Yarn conditioning process



Patented Apr. 9, 1940 UNITED STATES PATENT OFFICE 2,196,748 YARN CONDITIONING PRocEss .losephB. Dickey, Rochester, N. Y., assignor to Eastman Kodak Company, Rochester, N. Y., a corporation of New Jersey No Drawing. Application December 18, 1938, Serial No. 246,205

13 Claims.

strains and to lubricate the yarn in order to facilitate handling in such operations as spinning, twisting, winding and reeling. It is also necessary to treat yarn to adapt it for use as warp or filling or for the manufacture of various types of knitted fabrics. In knitting, it is particularly important that the yarn be soft and pliable in order that it may conform readily to the contour of the needles and thus produce a closely knit fabric free from such defects as 25 stitch distortion, "pin holes, laddering, and the like. 7

Heretofore it has been proposed to employ softening agents such as polyhydric alcohols and similar agents as ingredients of yarn conditioning or lubricating formulas, generally in connection with mineral, animal or vegetable oils. It has been found, however, that most of the known softening agents and the various formulas containing them have certain drawbacks, one of the most serious of which is high vapor pressure, and in some cases too drastic a solvent action on the yarn. Many of such agents possess slight or insuflicient solvent power for the lubricants with which they are used, and it is accordingly necessary to employ blending agents or emulsifying agents in order to obtain operable yarn treating formulas. In addition, many of the known softening and lubricating agents are insufliciently soluble in water to permit satisfactory removal by aqueous scour baths. 1

This invention has as its principal object to provide an entirely new class of yarn conditioning agents which are particularly adapted for the 50 organic derivatives of cellulose and capable of lubricating, softening and rendering such yarns more amenable to knitting and other textile operations. A further and specific object is to provide a class of conditioning agents which aug- 55 ment or assist the lubricating action of various lubricants when applied to such yarns. A still.

further object is to provide yarn softening and lubricating formulas which can be readily removed from the yarns by the usual scour baths.

so A still further object is to provide anjmproved when they are subjected to various mechanical method for the conditioning of yarns, particularly those composed of or containing organic derivatives of cellulose such as cellulose acetate, whereby the yarn is rendered soft and pliable and capable of employment in a variety of textile operations where complicated designs or stitches are employed. Another object is to provide an improved type of yarn which is especially amenable to textile operations including circular knitting, weaving, spinning and the like. Other objects will appear hereinafter.

These objects are accomplished by the following invention which, in its broader aspects, comprises the discovery that hydroxyalkoxy tetrahydrofurfuryl ethers having the formula:

where n is 1, 2, 3, etc., may be used as yarn conditioning agents and particularly as softening agents, with or without the addition of animal,

mineral, or vegetable oils, in the treatment of yarns composed of or containing organic derivatives of cellulose. I have found that these compounds when employed as described in the detailed examples set forth below have a slight solvent and/or softening action on cellulose organic derivative yarns which renders such yarns soft and pliable without at the same time having too drastic an action thereon.

The compounds indicated above can be prepared by heating tetrahydrofurfuryl alcohol with ethylene, an alkylene oxide such as propylene and butylene oxides glycidol and cyclohexene with or without a catalyst. Compounds of this type can be conveniently prepared for example; by reacting tetrahydrofurfuryl alcohol at temperatures varying from 100-250 with any desired quantity of ethylene oxide and with or without a suitable catalyst such as sulfuric acid, phosphoric acid, boric acid, acid aluminum fluorosilicate, boron trifluoride, and various salts such as sodium chloride, mono, di and tri-sodium phosphate, sodium hydroxide, calcium oxide, etc. By varying the ratio of alcohol to alkylene oxide the relative amounts of the various reaction products can be controlled. That is, if the compound: treatment of yarns composed of or .containing' is desired, I use 1 mole of alcoholto 0.5 l.5 of the oxide. In nearly all cases some of the poly ethers are formed. Of course, if poly ethers are desired, more ethylene oxide is used.

The preparation of these compounds is also carried out in the vapor phase. A stream of tetrahydrofurfuryl alcohol vapor containing the desired amount of ethylene oxide is passed through a heated tube (iron, copper, glass, quartz, etc.) which may contain a catalyst (such as those named above) supported on pumice or a naturally occurring catalyst such as 'fullers earth, Japanese earth, etc. The reaction'products are condensed and fractionated.

Examples of the preparation of typical compounds of this type are as follows:

PREPARATION or Comrotmns Example 1 700 gm. tetrahydrofurfuryl alcohol ('7 moles), 163 gm. ethylene oxide (3.7 moles), and 0.2 gm. boric acid are heated in a shaking autoclave at -165 for 12 hrs. The reaction product was distilled an'd'gave ethylene oxide, tetrahydrofurfuryl alcohol,.37% of B-hydroxyethyl tetrahydrofurfuryl ether, and 23-10% of a mixture of the higher ethers. By increasing the time of heating a higher yield of the last two reaction products is obtained. I

Example 2 Example 3 700 gmJtetrahydrofurfuryl alcohol, 330 gm. ethylene oxide, and 1 gm. phosphoric. acid are 'heated in an autoclave at ISO- for 24 hours and the reaction product is worked up as previously described. There is obtained ethylene oxide, tetrahydrofurfuryl alcohol, 40% yield of phydroxyethyl tetrahydrofurfuryl ether, 5% of B- hydroxy-p-ethoxyethyl tetrahydrofurfuryl ether, B. P. 135-140/3 mm. and smaller amounts of the next two higher ethers. phoric acid there may be used sulfuric acid, acid aluminum fiuorosilicate, fluorohoric acid, sodium chloride, Japanese clay, etc.

Example 4 700 gm. tetrahydrofurfuryl alcohol, 620 gm. ethylene oxide, and 2 gm. boric acid are heated in a shaking autoclave at 170-180" for 24 hours. The reaction products are then fractionated through an efflcient column and there are obtained some tetrahydrofurfuryl alcohol and good yields of the following ethers: p-hydroxyethyl tetrahydrofurfuryl ether; B-hydroxy-B-ethoxy tetrahydrofurfuryl ethyl ether; p-hydroxy-B'-ethoxy-;8-ethoxy tetrahydrofurfuryl ethyl etherethoxy p ethoxytetrahydrofurfurylethyl. ether, B. P. 195/3 mm.,

and a small amount of higher boiling ethers and tar.

In place of phos- 7 Example 5 A stream of nitrogen gas saturated with tetrahydrofurfurylalcohol and ethylene oxide (1-'1) is passed through a glass tube (3 ft. long) heated -to 170 and the escaping gases are condensed. The reaction products are fractionated to give ethylene oxide, tetrahydrofurfuryl alcohol, a-hydroxyethyl tetrahydrofurfuryl ether, and smaller amounts of the products given in Example 4.

Example 6 A stream of ethylene oxide vapor (heated to 100) saturated with tetrahydrofurfuryl alcohol is passed through a glass tube heated to 170-180 and filled with pumice saturated with boric acid. The reaction products are Worked up as previously described and the ethers listed in Example 4 are obtained. In place of boric acid supported on pumice there may be used any of the catalysts previously mentioned.

In accordance with the invention these compounds may be applied directly to the yarn during or after spinning, or may be added to the spinning solution itself. I have found that these compounds have exceptional solvent powers which enable them to dissolve mineral oils and blown and unblown, drying and semi-drying, vegetable and animal oils and accordingly they may be, and preferably are, employed as ingredients of yarn conditioning or lubricating formulas in conjunction with agents which function wholly or partially as'lubricant's.

In the following examples and description I have set forth several of the preferred embodiments of my invention, but they are included merely for purposes of illustration and not as a limitation thereof.

My invention will be more readily understood by reference to the following examples in which typical applications of the invention are set forth.

Example 7 The compound:

mc-cH,

H2 cn-omooinororr is applied to textile materials (silk, wool, viscose,

cotton, cellulose acetate) by means of a wick,-

roller, spray, bath, pad, etc. to facilitate their knitting, weaving, spinning and the like. If the yarn is intended primarily for knitting, the amount of conditioning liquid applied may vary from 4-25% by weight of the yarn and if for weaving between 1-5% by weight of the yarn.

and applied to textile materials such as silk, wool, cellulose acetate, viscose, etc. as described in Example 1. If the yarn is intended primarily for knitting, the amount of conditioning liquid applied may vary from 4-25% by weight of the yarn and if for weaving, from 1-,5% by weight of the yarn. Cellulose derivative filaments or fibers treated as described are quite soft and pliable and give improved results in various operations such as weaving, knitting, etc.

Other examples of yarn conditioning compo- Example 9 CH5-CH: P8115 OH: CH-CHr-(O CnHdi-OH 60 Blown olive oil.-. 40

Example 10 ([JH,CH: Parts CH1 CH-CHr-(O Calms-OH 20 Light mineral oil 80 Example 11 (Elly-CH2 Parts CH: CH-CHzclmon 20 Blown sperm oil 80 Example 12 H2C-CH: Parts H2C\ CH-OH:0 C lLOH 40 Neat's-ioot oil 60 Example 13 CH:CH: Parts CH: H-CBr-(O CzH4)4-0H 20 Blown '1 il 30 Sulfonated soya bean oil 20 White mineral 10 01810 110i! 10 Et'mmnlaminn 3 Water 7 Example 14 CH:CHI PBi'tS H: CH-CHz-(O ClH4)aOH 20 O Sperm oil 60 Clay} nlmhnl 20 Example -15 (HIP-C H: Part s CH: H-CHr-(OC2H4)r-0H 20 Diglyceryl acetone 20 sitions which may be applied to various types of yarns, particularly those composed of or containing cellulose acetate, cellulose acetate propionate, cellulose acetate butyrate, and similar cellulose organic acid esters in accordance with my invention and which render such yarns soft and pliable and especially well adapted for various textile operations, particularly knitting, are as follows:

Blown soya bean 60 thus produced are pliable and suitable for knitting.

Example 17 Parts Water 80 CHa-CH; H: HrCHr-(O C2114) 2-0H 10 Water soluble cellulose ester;

Glycerol acetone 5 Any of the above compositions may be applied to the yarn intended for use in circular knitting by means of a bath, wick, spray, roller, pad or any suitable means. The amount of conditioning liquid applied may vary between 5-25% by weight of the yarn. Usually, however, the amount of conditioning liquid applied is about -15% by Weight of the yarn. Yarn composed of cellulose acetate conditioned as described above gives excellent results when used in the circular knitting process.

As .will be apparent from the above, examples and description the conditioning agents of my invention may be applied by a wide variety of methods. For example, I may employ the agent as an ingredient of the spinning dope from which the yarn after spinning, this may be done by bringing the yarn in contact with a wick, rol or felt wet therewith, or; the liquid may be applied by immersion, spray, or otherwise. The particular point at which the liquid is applied may vary. It may, for example, be applied to the yarn inside or outside the spinning cabinet, between the guide and godet roll, between the godet or other roll or guide and the point of winding and/or twisting. In some cases, the liquid may even be applied to the yarn after winding onto cones, spools, bobbins, or the like or by the so-' called bobbin to bobbin method. In the case of staple fiber manufacture, the liquid may be applied to the yarn prior to, or, after cutting into staple lengths.

The amount of the fluid so employed will vary widely-depending upon the results desired, the specific nature of the material to which the agent is applied, the use to which the yarn is eventually to be put and other factors. For example, in a given case where a cellulose organic acid ester yarn such as a yarn composed of cellulose acetate, is intended for knitting, about 4 to or more by weight, based on the weight of the dry yarn, may be satisfactory, while if the yarn is intended for weaving, the amount may vary between about 1 and 5%.

Although in the above examples I have referred primarily to yarn treating compositions containing only the conditioning agent and an oil, other ingredients such as solvents, non-solvents, emulsifying agents, blending agents and the like, may

be added within the scope of my invention. Likewise, various dyes or other coloringmatter may be included in case it is desired to permanently or fugitively tint or dye the material undergoing treatment.

Although I have found it convenient to illustrate'my invention by reference to compositions containing specific percentages of the various ingredients, these percentages may vary widely depending upon the particular purpose for which the composition is intended. For example, if it is desired to control the solvent; or softening action of the conditioning agent, the amount of the agent may be adjustedas, for example, by reducing the amount of the agent and corresponds ingly increasing the amount of oil or other ingradient.

While I have described my invention withparticular reference to the treatment of yarns composed of organic derivatives of cellulose such as cellulose acetate, the conditioning agents and formulas described herein are applicable to the conditioning of many other types of cellulose derivative yarns such as those composed of or containing cellulose propionate, cellulosebutyrate, cellulose acetate propionate, cellulose acetate butyrate, ethyl cellulose, methyl cellulose, benzyl cellulose and others, as well as to theconditioning of silk, wool, cotton, viscose and other natural or artificial materials.

The term yarn as used herein and in the claims is to be understood as including a single filament, a plurality of filaments associated into the form of a thread, either of high or low twist, single or multiple threads associated or twisted together, composite threads composed of a mixture of natural and artificial filaments or a composite thread formed by twisting together individual strands of natural or artificial materials, as well as cut staple fibers produced from natural and/or artificial filaments or threads and spun yarn produced from such staple fibers.

As indicated above, the yarn conditioning agents of my invention are exceptionally good solvents for a wide variety of mineral, blown and unblown, drying and semi-drying animal and vegetable oils such as cottonseed, olive, castor, neats-foot, sperm and other oils. This enables them to be used with any of such oils in makin up a variety of yarn treating formulas of varying composition.

The yarn conditioning method and compositions of my invention possess many outstanding advantages. The fundamental and outstanding characteristic of the agents employed in accordance with the invention is their ability to soften yarns, especially those composed of or containing organic derivatives of cellulose such as cellulose acetate and render them soft and pliable and amenable to various textile operations, especially operations such as those involved in weavin and knitting where complicated designs or stitches are employed, without too drastic an action on the yarn material. Another outstanding characteristic of these compounds is their exceptional solvent power for a wide variety of mineral, animal, and vegetable oils and their ability to act as lubricating assistants in conjunction with these oils when applied to such yarns. Inaddition, due to their solubility in water, they may be readily removed from yarns and fabrics by means of the usual aqueous scour baths. By employing the yarn conditioning agents and method of my invention as herein described, one is enabled to obtain highly satisfactory results in'the manufacture of yarns and woven fabrics and especially the production from these yarns of closely knit fabrics free from defects such as pin holes, stitch distortion, laddering and the like.

What I claim and desire to secure by Letters Patent of the United States is:

1; The process of conditioning yarn to rende it more amenable to textile operations including knitting, weaving, spinning and the like, which comprises applying thereto a lubricating and softening composition containing as its essential lubricating and softening component hydroxyalkoxy tetrahydrofurfuryl ether having the formula:

HzC CH! mo CHCHz(0-alkyl)..-OH

o where n is a small whole number at least one.

2. The process of conditioning yarn composed of or containing organic derivatives of cellulose to render it more amenable to textile operations including knitting, weaving, spinning and the like, which comprises applying thereto a lubricating and softening composition containing as its essential lubricating and softening component a hydroxyalkoxy tetrahydrofurfuryl ether haying the formula:

where n isa small whole number at least one.

3. The process of conditioning yarn composed of or containing cellulose acetate to render it more amenable to textile operations including knitting, weaving, spinning, and the like, which comprises applying thereto a lubricating and softening composition containing as its essential lubricating and softening component a hydroxyalkoxy tetrahydrofurfuryl ether having the formula:

where n is a small whole number at least one.

4. The process of conditioning yarn composed of or containing cellulose acetate to render it more amenable to textile operations including knitting, weaving, spinning, and the like, which comprises applying thereto a lubricating and softening composition containing as its essential lubricating and softening component a hydroxyalkoxy tetrahydrofiurfuryl ether having the formula:

where n is a small Whole number at least one, and a textile lubricant.

5. The process of conditioning yarn composed of or containing cellulose acetate to render it more amenable to textile operations including knitting, weaving, spinning, and the like, which comprises applying thereto a lubricating and softening composition containing as its essential lubricating and softening component ,S-hydroxy tetraethylene glycol tetrahydrofurfuryl ether.

6. The process of conditioning yarn composed of or containing cellulose acetate to render it more amenable to textile operations including knitting, weaving, spinning, and the like, which comprises applying thereto a lubricating and softening composition containing as its essential lubricating and softening component 8- hydroxy triethylene glycol tetrahydrofurfuryl 4 ether. I

as its essential lubricating and softening component a hydroxyalkoxy tetrahydrofurturyl ether having the formula:

where n is a smallv whole number at least one.

10. Textile yarns composed of or containing organic derivatives of cellulose amenable to textile operationsincluding knitting, weaving, spinning, and the like impregnated with a conditioning agent comprising a hydroxyalkoxy tetrahydrofuryl ether having the formula:

where n is a small whole number at least one, and a textile lubricant.

11. Textile yarns composed of or containing cellulose acetate amenable to textile operations including knitting, weaving, spinning, and the like, impregnated with a lubricant comprising B-hydroxy tetraethylene glycol tetrahydrofurfuryl ether.

12. Textile yarns composed of or containing cellulose acetate amenable to textile operations including knitting, weaving, spinning, and the like, impregnated with a lubricant comprising fl-hydroxy triethylene glycol tetrahydrofurfuryl ether.

13. Textile yarns composed of or containing cellulose acetate amenable to textile operations including knitting, weaving, spinning, and the like, impregnated with a lubricant p-hydro w diethylene glycol tetrahydrofurfuryl ether.

. JOSEPH B. DICKEY. 

